WO2018180709A1 - Composé, dispositif électronique le contenant, élément électroluminescent à film mince organique, dispositif d'affichage et dispositif d'éclairage - Google Patents

Composé, dispositif électronique le contenant, élément électroluminescent à film mince organique, dispositif d'affichage et dispositif d'éclairage Download PDF

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WO2018180709A1
WO2018180709A1 PCT/JP2018/010824 JP2018010824W WO2018180709A1 WO 2018180709 A1 WO2018180709 A1 WO 2018180709A1 JP 2018010824 W JP2018010824 W JP 2018010824W WO 2018180709 A1 WO2018180709 A1 WO 2018180709A1
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group
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compound
substituted
general formula
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PCT/JP2018/010824
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徳田貴士
田中大作
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東レ株式会社
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Priority to JP2018515691A priority Critical patent/JP6954275B2/ja
Priority to KR1020197026760A priority patent/KR102514842B1/ko
Priority to CN201880017449.5A priority patent/CN110392682B/zh
Publication of WO2018180709A1 publication Critical patent/WO2018180709A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/167—Electron transporting layers between the light-emitting layer and the anode

Definitions

  • the present invention relates to a compound, an electronic device containing the compound, an organic thin film light emitting element, a display device, and a lighting device.
  • An organic thin film light-emitting element is an element that emits light when electrons injected from a cathode and holes injected from an anode are recombined in an organic phosphor sandwiched between the two electrodes.
  • Organic thin-film light-emitting devices are thin, can emit light with high brightness under low driving voltage, and can emit multicolor light by properly selecting light-emitting materials such as fluorescent light-emitting materials and phosphorescent light-emitting materials It is a feature.
  • organic thin-film light-emitting elements have been steadily put into practical use, such as being used in the main display of mobile phones.
  • the existing organic thin film light emitting devices still have many technical problems.
  • achieving both high-efficiency light emission and extending the life of the organic thin-film light-emitting element is a major issue.
  • nitrogen-containing aromatic heterocycle compounds in which a carbazole skeleton is linked to a quinazoline skeleton that is a heteroaromatic ring containing a nitrogen atom (hereinafter referred to as “nitrogen-containing aromatic heterocycle”) have been developed (for example, Patent Documents 1-2 and Non-Patent Document 1).
  • An object of the present invention is to provide an organic thin-film light-emitting element that solves the problems of the prior art and has improved luminous efficiency, driving voltage, and durability life.
  • the present invention is a compound represented by the following general formula (1).
  • L 1 and L 2 are a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
  • L 1 is linked at any one position among X 1 to X 8 and R 55
  • L 2 is linked at any one position among X 9 to X 16 and R 56 .
  • L 1 is connected at the position of R 55 and L 2 is connected at the position of R 56 .
  • Either L 1 or L 2 is necessarily a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.
  • R 51 to R 54 are each independently a hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, aryl Selected from the group consisting of a group, a heteroaryl group, a halogen atom, a cyano group, an amino group, a carbonyl group, a carboxy group, an oxycarbonyl group, a carbamoyl group, and —P ( ⁇ O) R 57 R 58 .
  • R 57 and R 58 are an aryl group or a heteroaryl group, and R 57 and R 58 may be condensed to form a ring.
  • R 55 and R 56 are selected from the group consisting of a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an aryl group, and a heteroaryl group.
  • R 17 and R 18 are an aryl group or a heteroaryl group, and R 17 and R 18 may be condensed to form a ring.
  • an organic thin film light emitting device excellent in terms of high luminous efficiency, low driving voltage and long durability life.
  • L 1 and L 2 are a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
  • L 1 is linked at any one position among X 1 to X 8 and R 55
  • L 2 is linked at any one position among X 9 to X 16 and R 56 .
  • L 1 is connected at the position of R 55 and L 2 is connected at the position of R 56 .
  • Either L 1 or L 2 is necessarily a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.
  • R 51 to R 54 are each independently a hydrogen atom, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl ether group, aryl thioether group, aryl Selected from the group consisting of a group, a heteroaryl group, a halogen atom, a cyano group, an amino group, a carbonyl group, a carboxy group, an oxycarbonyl group, a carbamoyl group, and —P ( ⁇ O) R 57 R 58 .
  • R 57 and R 58 are an aryl group or a heteroaryl group, and R 57 and R 58 may be condensed to form a ring.
  • R 55 and R 56 are selected from the group consisting of a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an aryl group, and a heteroaryl group.
  • R 17 and R 18 are an aryl group or a heteroaryl group, and R 17 and R 18 may be condensed to form a ring.
  • hydrogen may be deuterium.
  • a substituted or unsubstituted aryl group having 6 to 40 carbon atoms is 6 to 40 carbon atoms including the number of carbon atoms contained in the substituent group substituted on the aryl group. The same applies to other substituents that define the number of carbon atoms.
  • substituents include the alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, aryl as described above.
  • An ether group, an arylthioether group, an aryl group, a heteroaryl group, a halogen atom, a cyano group, an amino group, a carbonyl group, a carboxy group, an oxycarbonyl group, and a carbamoyl group are preferred, and further preferred in the description of each substituent. Specific substituents are preferred. Moreover, these substituents may be further substituted with the above-mentioned substituents.
  • the alkyl group represents, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, or a tert-butyl group.
  • the alkyl group may or may not have a substituent. There is no restriction
  • the number of carbon atoms of the alkyl group is not particularly limited, but is preferably in the range of 1 to 20 and more preferably 1 to 8 from the viewpoint of availability and cost.
  • the cycloalkyl group represents a saturated alicyclic hydrocarbon group such as a cyclopropyl group, a cyclohexyl group, a norbornyl group, an adamantyl group, and the like.
  • the cycloalkyl group may or may not have a substituent.
  • the carbon number of the alkyl group moiety in the cycloalkyl group is not particularly limited, but is preferably in the range of 3 or more and 20 or less.
  • the heterocyclic group refers to an aliphatic ring having an atom other than carbon, such as a pyran ring, a piperidine ring, or a cyclic amide.
  • the heterocyclic group may or may not have a substituent.
  • the heterocyclic ring may have one or more double bonds in the ring as long as it does not have aromaticity.
  • carbon number of a heterocyclic group is not specifically limited, Preferably it is the range of 2-20.
  • alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, or a butadienyl group.
  • the alkenyl group may or may not have a substituent.
  • carbon number of an alkenyl group is not specifically limited, Preferably it is the range of 2-20.
  • the cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexenyl group.
  • the cycloalkenyl group may or may not have a substituent.
  • carbon number of a cycloalkenyl group is not specifically limited, Preferably it is the range of 4-20.
  • An alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as an ethynyl group.
  • the alkynyl group may or may not have a substituent.
  • carbon number of an alkynyl group is not specifically limited, Preferably it is the range of 2-20.
  • An alkoxy group refers to a functional group in which an aliphatic hydrocarbon group is bonded via an ether bond, such as a methoxy group, an ethoxy group, or a propoxy group.
  • This aliphatic hydrocarbon group may or may not have a substituent.
  • carbon number of an alkoxy group is not specifically limited, Preferably it is the range of 1-20.
  • the alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom.
  • the hydrocarbon group of the alkylthio group may or may not have a substituent. Although carbon number of an alkylthio group is not specifically limited, Preferably it is the range of 1-20.
  • An aryl ether group refers to a functional group to which an aromatic hydrocarbon group is bonded via an ether bond, such as a phenoxy group. This aromatic hydrocarbon group may or may not have a substituent. Although carbon number of an aryl ether group is not specifically limited, Preferably, it is the range of 6-40.
  • the aryl thioether group is a group in which an oxygen atom of an ether bond of an aryl ether group is substituted with a sulfur atom.
  • the aromatic hydrocarbon group in the aryl thioether group may or may not have a substituent.
  • the number of carbon atoms of the arylthioether group is not particularly limited, but is preferably in the range of 6 or more and 40 or less.
  • the aryl group represents an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a phenanthryl group, an anthracenyl group, a pyrenyl group, or a fluoranthenyl group.
  • the aryl group may or may not have a substituent.
  • carbon number of an aryl group is not specifically limited, Preferably, it is the range of 6-40, More preferably, it is the range of 6-24.
  • Specific examples of the aryl group are preferably a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.
  • a heteroaryl group is a furanyl group, thiophenyl group, pyridyl group, quinolinyl group, isoquinolinyl group, pyrazinyl group, pyrimidyl group, naphthyridyl group, benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, dibenzothiophenyl group And a cyclic aromatic group having one or more atoms other than carbon, such as a carbazolyl group, in the ring.
  • the heteroaryl group may or may not have a substituent. Although carbon number of heteroaryl group is not specifically limited, Preferably it is the range of 2-30. Specific examples of the heteroaryl group are preferably a pyridyl group, a quinolyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.
  • An amino group is a substituted or unsubstituted amino group.
  • substituent in the case of substitution include an aryl group, a heteroaryl group, a linear alkyl group, and a branched alkyl group. More specifically, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a methyl group and the like can be mentioned, and these substituents may be further substituted.
  • carbon number of a substituent is not specifically limited, Preferably, it is the range of 6-40.
  • the halogen atom is an atom selected from fluorine, chlorine, bromine and iodine.
  • the carbonyl group, carboxy group, oxycarbonyl group, carbamoyl group and phosphine oxide group may or may not have a substituent.
  • substituents include an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group, and these substituents may be further substituted.
  • Arylene group refers to a divalent or higher valent group derived from an aromatic hydrocarbon group such as benzene, naphthalene, biphenyl, fluorene, phenanthrene.
  • the arylene group may or may not have a substituent.
  • Preferred arylene groups are divalent or trivalent arylene groups. Specific examples of the arylene group include a phenylene group, a biphenylene group, a naphthylene group, and a fluorenylene group.
  • 1,4-phenylene group 1,3-phenylene group, 1,2-phenylene group, 4,4′-biphenylene group, 4,3′-biphenylene group, 3,3′-biphenylene group 1,4-naphthalenylene group, 1,5-naphthalenylene group, 2,5-naphthalenylene group, 2,6-naphthalenylene group, 2,7-naphthalenylene group, 1,3,5-phenylene group and the like. More preferred are 1,4-phenylene group, 1,3-phenylene group, 4,4'-biphenylene group, and 4,3'-biphenylene group.
  • a heteroarylene group is a divalent or higher valent group derived from an aromatic group having one or more atoms other than carbon, such as pyridine, quinoline, pyrimidine, pyrazine, triazine, quinoxaline, quinazoline, dibenzofuran, dibenzothiophene. The group of is shown.
  • the heteroarylene group may or may not have a substituent.
  • Preferred heteroarylene groups are divalent or trivalent heteroarylene groups. Although carbon number of heteroarylene group is not specifically limited, Preferably it is the range of 2-30.
  • heteroarylene group examples include 2,6-pyridylene group, 2,5-pyridylene group, 2,4-pyridylene group, 3,5-pyridylene group, 3,6-pyridylene group, 2,4, 6-pyridylene group, 2,4-pyrimidinylene group, 2,5-pyrimidinylene group, 4,6-pyrimidinylene group, 2,4,6-pyrimidinylene group, 2,4,6-triazinylene group, 4,6-dibenzofurani
  • Examples include a len group, a 2,6-dibenzofuranylene group, a 2,8-dibenzofuranylene group, and a 3,7-dibenzofuranylene group.
  • the quinazoline skeleton Since the quinazoline skeleton has two nitrogen atoms that form sp 2 hybrid orbitals with high electronegativity, it has a high affinity with electrons and a high electron transport property. Therefore, when a compound having a quinazoline skeleton is used for the electron injection layer of the organic thin film light emitting device, electron injection from the cathode to the electron injection layer is likely to occur.
  • the electron transport layer exhibits high electron transport properties.
  • the LUMO energy level of a molecule consisting only of a quinazoline skeleton is too low compared to the lowest empty orbital (LUMO) energy level of the light emitting layer. This hinders electron injection from the electron transport layer to the light emitting layer.
  • a carbazole skeleton is introduced into the compound represented by the general formula (1). This is because the carbazole skeleton has a property of increasing the LUMO energy level and a good electron transport property.
  • a carbazole skeleton By introducing a carbazole skeleton into a compound having a quinazoline skeleton, a low LUMO energy level derived from the quinazoline skeleton is increased. Therefore, when such a compound is used for the electron transport layer, the electron injection into the light emitting layer can be enhanced.
  • the carbazole skeleton and quinazoline skeleton have a property of high charge transportability in the skeleton.
  • the highest occupied orbital (HOMO) and LUMO spread in the molecule.
  • the overlap of orbits with adjacent molecules also increases, improving the charge transport property.
  • the compound represented by the general formula (1) is used in any of the layers constituting the organic thin film light emitting device, electrons generated from the cathode and holes generated from the anode can be efficiently transported, The driving voltage of the organic thin film light emitting element can be lowered. As a result, the luminous efficiency of the organic thin film light emitting element can be improved.
  • the molecular orbitals are widened, so that radicals generated when charges are received are stabilized.
  • the carbazole skeleton and the quinazoline skeleton have high stability against electric charges, that is, electrochemical stability. Therefore, when the compound represented by the general formula (1) is used for any layer constituting the organic thin film light emitting element, the durability life of the organic thin film light emitting element is improved.
  • the carbazole skeleton and quinazoline skeleton each have a rigid structure in which a plurality of rings are condensed. Therefore, the compounds having these skeletons exhibit a high glass transition temperature. Further, when such a compound is sublimated, due to its rigid structure, each molecule is not entangled and is stably sublimated. Thus, since the glass transition temperature of the compound represented by General formula (1) is high, the heat resistance of an organic thin film light emitting element improves. Moreover, since the good quality film
  • the compound represented by the general formula (1) has two carbazole skeletons and a quinazoline skeleton in the molecule, so that all of high luminous efficiency, low driving voltage, and long durability life are possible. .
  • the compound represented by the general formula (1) is preferably used for a light emitting layer or an electron transport layer of an organic thin film light emitting device, and particularly preferably used for an electron transport layer.
  • L 1 is linked at any one position among X 1 to X 8 and R 55
  • L 2 is linked at any one position among X 9 to X 16 and R 56. .
  • the coupling with L 1 is the position of the X 1, but X 1 is C-R 1, R 1 itself is not present, means that L 1 and the carbon atom is attached directly.
  • L 1 is a linking at the position of R 55, R 55 itself is absent, carbazole - nitrogen atom of Le backbone and the L 1 means a direct binding.
  • the positions of L 1 and L 2 of the quinazoline skeleton are substitution positions on a six-membered ring having an electron-attracting nitrogen atom in the quinazoline skeleton.
  • the low LUMO energy level derived from the quinazoline skeleton is distributed on a six-membered ring having an electron withdrawing nitrogen atom. Therefore, bonding a carbazole skeleton at this position has a great effect of increasing the LUMO energy level of the compound. Thereby, the electronic injection can be increased as described above.
  • L ⁇ 1 > connects at the position of X ⁇ 3 >. Further, it is preferable that L 2 is connected at the position of X 14. This is because the effect of increasing the LUMO energy level of the compound is particularly great when linked at these positions.
  • L 1 is connected at the position of R 55 and L 2 is connected at the position of R 56 .
  • the quinazoline skeleton is linked to the nitrogen atom of the carbazole skeleton, the effect of increasing the LUMO energy level of the compound is small.
  • the effect of increasing the LUMO energy level of the compound can be maintained.
  • both of the two carbazole skeletons are linked by the nitrogen atom and the quinazoline skeleton, the effect cannot be maintained, so that the electron injection force of the compound becomes small.
  • L 1 or L 2 is necessarily a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group. This is because the molecules become more rigid, the glass transition temperature becomes higher, and the heat resistance of the organic thin film light emitting device is improved.
  • L 1 and L 2 are a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.
  • the substituent is as described above, and preferably an alkyl group, a cycloalkyl group, a heterocyclic group, an aryl ether group, an aryl A thioether group, an aryl group, a heteroaryl group, a halogen atom, a cyano group, or an amino group, more preferably a heterocyclic group, an aryl group, a heteroaryl group, a halogen atom, a cyano group, or an amino group; An aryl group, a heteroaryl group, or an amino group is preferable.
  • L 1 and L 2 are more preferably a single bond and an arylene group having 6 to 24 carbon atoms, and still more preferably a single bond and a phenyl group.
  • L 1 and L 2 are connecting groups that form around the quinazoline skeleton that forms the LUMO level, which is an electron conduction level. Therefore, a single bond and an arylene group that have a small influence on the LUMO level of quinazoline are preferable.
  • a single bond and a phenyl group that are small in size and have a higher electron transport property between molecules are more preferable.
  • L 1 is preferably a single bond
  • L 2 is preferably a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.
  • L 2 is preferably a substituted or unsubstituted arylene group, and more preferably L 2 is a substituted or unsubstituted phenylene group.
  • L 2 is preferably a single bond
  • L 1 is preferably a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group.
  • L 1 is preferably a substituted or unsubstituted arylene group
  • L 1 is more preferably a substituted or unsubstituted phenylene group.
  • L 1 and L 2 When only one of L 1 and L 2 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, the effect of increasing the LUMO energy level due to the bond of the carbazole skeleton is increased. It is.
  • Substituents other than hydrogen atoms are introduced to modify the electronic state of the carbazole skeleton.
  • an aromatic heterocyclic group containing an oxygen atom hereinafter referred to as “oxygen-containing aromatic heterocyclic group”
  • an aromatic heterocyclic group containing a sulfur atom hereinafter referred to as “sulfur-containing aromatic heterocyclic group”
  • the electron-donating substituent reinforces the electron-donating property of the carbazole skeleton.
  • an electron withdrawing substituent such as a cyano group decreases the electron donating property of the carbazole skeleton.
  • R 51 to R 54 are as described above, but preferably a hydrogen atom, a cycloalkyl group, a heterocyclic group, an aryl ether group, an aryl thioether group, an aryl group, a heteroaryl group, a halogen atom, a cyano group, and an amino group. More preferably a hydrogen atom, an aryl group, a heteroaryl group, a halogen atom, a cyano group, and an amino group, and particularly preferably a hydrogen atom.
  • R 55 and R 56 are as described above, and preferably an aryl group.
  • the LUMO energy level of the compound represented by the general formula (1) is slightly lower than the LUMO energy level of a material having an anthracene skeleton, which is often used as a host material of a blue light emitting layer. Therefore, in the organic thin film light emitting device, it is preferable to use a compound having an anthracene skeleton for the light emitting layer, particularly the blue light emitting layer, and use the compound represented by the general formula (1) for the electron transport layer or the electron injection layer. In such an organic thin film light emitting element, electron injection into the blue light emitting layer is moderately suppressed. Accordingly, the inside of the light emitting layer is prevented from being in an electron-excess state, and the carrier balance is adjusted. Thereby, the luminous efficiency and the durability life of the organic thin film light emitting element are improved.
  • the compound represented by the general formula (1) easily receives electrons from a compound having a pyrene skeleton, a phenanthroline skeleton, or a fluoranthene skeleton. These compounds can transport electrons even when the organic thin film light emitting device is driven at a low voltage. Therefore, in the organic thin film light-emitting element, a compound having a pyrene skeleton, a compound having a phenanthroline skeleton, or a compound having a fluoranthene skeleton is used in a layer in contact with the cathode side of the layer containing the compound represented by the general formula (1). Is preferred. Such an organic thin film light emitting device can be driven at a low voltage.
  • the compound having a pyrene skeleton has a substituted or unsubstituted aryl group or heteroaryl group at the 1- and 6-positions because the electron transport property is increased.
  • the compound having a phenanthroline skeleton has a plurality of phenanthroline skeletons in the molecule in order to disperse electric charges and accelerate electron transfer.
  • the compound having a fluoranthene skeleton is more preferably a compound having a fluoranthene skeleton and an amino group in order to increase the deep LUMO energy of the fluoranthene skeleton.
  • the compound represented by the general formula (1) is not particularly limited, but specific examples include the following.
  • a well-known method can be utilized for the synthesis
  • a carbazole skeleton having a halogen atom or boronic acid bonded thereto is commercially available.
  • the synthesis method include a method using a coupling reaction between a substituted or unsubstituted carbazolylboronic acid derivative and a substituted or unsubstituted halogenated quinazoline derivative under a palladium catalyst or a nickel catalyst, Alternatively, a method using a coupling reaction between an unsubstituted carbazole derivative and a substituted or unsubstituted halogenated quinazoline derivative, or a substituted or unsubstituted halogenated carbazole derivative and a substituted or unsubstituted quinazolinylboronic acid derivative However, it is not limited to these methods.
  • Boronic acid esters may be used instead of boronic acid.
  • the halogen atom bonded to the carbazole skeleton can be converted into a boronic acid ester using a known method.
  • the quinazoline skeleton can be synthesized by a cyclization reaction from a substituted or unsubstituted 2-aminobenzonitrile derivative and a Grignard reagent using a known method. Halogenated quinazolines are commercially available and can be used.
  • L 1 and L 2 having a quinazoline skeleton have higher reactivity of L 1 . Therefore, the carbazole binding reaction to quinazoline can be performed regioselectively by appropriately selecting the catalyst and the reaction temperature.
  • the compound represented by the general formula (1) is preferably used as an electronic device material in an electronic device such as an organic thin film light emitting device, a photoelectric conversion device, a lithium ion battery, a fuel cell, and a transistor. Among them, it is particularly preferable to be used as a light emitting element material in an organic thin film light emitting element.
  • a photoelectric conversion element is an element having an anode and a cathode and an organic layer interposed between the anode and the cathode.
  • the organic layer has a photoelectric conversion layer that converts light energy into an electrical signal. Since the compound represented by the general formula (1) has excellent electron transport properties, it is preferably used for the photoelectric conversion layer, and more preferably used for the n-type material of the photoelectric conversion layer.
  • the light emitting element material represents a material used for any layer of the organic thin film light emitting element.
  • the light-emitting element material is a material used for a layer selected from a hole transport layer, a light-emitting layer, and an electron transport layer, as well as a material used for an electrode protective layer (cap layer). included.
  • the organic thin film light-emitting element according to the embodiment of the present invention includes an anode, a cathode, and an organic layer interposed between the anode and the cathode, and the organic layer emits light by electric energy.
  • the organic layer preferably has at least a light emitting layer and an electron transport layer.
  • the organic layer in addition to the configuration of the light-emitting layer / electron transport layer, 1) hole transport layer / light-emitting layer / electron transport layer, 2) hole transport layer / light-emitting layer / electron transport layer / electron injection Layers, 3) Laminated configurations such as hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer, and the like.
  • Each of the layers may be a single layer or a plurality of layers.
  • a laminated type having a plurality of phosphorescent light emitting layers and fluorescent light emitting layers may be used, or a structure in which a fluorescent light emitting layer and a phosphorescent light emitting layer are combined may be used.
  • stacked the light emitting layer which shows mutually different luminescent color may be sufficient.
  • the element configuration described above may be a tandem configuration in which a plurality of layers are stacked via an intermediate layer. At least one of the organic layers included in the tandem structure is preferably a phosphorescent light emitting layer.
  • the intermediate layer is generally also referred to as an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer.
  • Specific examples of the tandem type structure include, for example, 1) hole transport layer / light emitting layer / electron transport layer / charge generation layer / hole transport layer / light emitting layer / electron transport layer, and 2) hole injection layer / hole transport.
  • a laminated structure including a generation layer can be given.
  • pyridine derivatives, phenanthroline derivatives and the like are preferably used as the material constituting the intermediate layer.
  • the phenanthroline derivative is more preferably a compound having two or more phenanthroline skeletons in the molecule.
  • the organic thin film light emitting device of the present invention contains a compound represented by the general formula (1) in the organic layer.
  • the compound represented by the general formula (1) may be used in any layer in the above device configuration, but has high electron injection and transport ability, fluorescence quantum yield, and thin film stability. It is preferably used for a light emitting layer, an electron transport layer or an intermediate layer of a light emitting element.
  • the compound represented by the general formula (1) is more preferably used for an electron transporting layer or an intermediate layer, and particularly preferably used for an electron transporting layer.
  • a substrate In order to maintain the mechanical strength of the light emitting element, it is preferable to form the light emitting element on a substrate.
  • a glass substrate such as soda glass or non-alkali glass is preferably used.
  • the thickness of the glass substrate it is sufficient that the thickness is sufficient to maintain the mechanical strength.
  • alkali-free glass is preferred because it is better that there are fewer ions eluted from the glass.
  • soda lime glass provided with a barrier coat such as SiO 2 is commercially available and can be used.
  • substrate does not need to be glass, For example, a plastic substrate may be sufficient.
  • the anode and the cathode have a role for supplying a sufficient current for light emission of the device.
  • at least one of the anode and the cathode is preferably transparent or translucent.
  • the anode formed on the substrate is a transparent electrode.
  • the material used for the anode is not particularly limited as long as it is a material that can efficiently inject holes into the organic layer and is transparent or translucent so that light can be extracted.
  • the material include conductive metal oxides such as tin oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO), metals such as gold, silver, and chromium, copper iodide, and copper sulfide.
  • conductive metal oxides such as tin oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO)
  • metals such as gold, silver, and chromium, copper iodide, and copper sulfide.
  • examples include inorganic conductive materials, conductive polymers such as polythiophene, polypyrrole, and polyaniline. These electrode materials may be used alone, or a plurality of materials may be laminated or mixed.
  • the substrate on which the anode is formed it is particularly preferable to use ITO glass in which an ITO film is formed on the glass surface, or Nesa glass in which a film containing tin oxide as a main component is formed on the glass surface.
  • the method for forming the ITO film is not particularly limited as long as the ITO film can be formed, such as an electron beam method, a sputtering method, and a chemical reaction method.
  • the material used for the cathode is not particularly limited as long as it can efficiently inject electrons into the light emitting layer.
  • the materials include metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, and these metals and low work function metals such as lithium, sodium, potassium, calcium and magnesium. Alloys or multilayer laminates are preferred.
  • the main component of the material used for the cathode is preferably aluminum, silver, or magnesium from the viewpoints of low electrical resistance, ease of film formation, film stability, luminous efficiency, and the like.
  • the cathode is made of magnesium and silver because electron injection into the electron transport layer and the electron injection layer is facilitated and the light emitting element can be driven at a lower voltage.
  • the method for producing these electrodes is not particularly limited, and examples thereof include resistance heating, electron beam, sputtering, ion plating, and coating.
  • a protective film layer In order to protect the cathode, it is preferable to laminate a protective film layer (cap layer) on the cathode.
  • a material which comprises a protective film layer For example, metals, such as platinum, gold
  • the compound represented by General formula (1) can also be utilized as this protective film layer.
  • a material used for the protective film layer is selected from materials that transmit light in the visible light region.
  • the hole transport layer is formed by a method of laminating or mixing one or more hole transport materials or a method using a mixture of a hole transport material and a polymer binder. Further, the hole transport material is required to efficiently transport holes injected from the anode between electrodes to which an electric field is applied. Therefore, as the hole transport material, a material having high hole injection efficiency and capable of efficiently transporting the injected holes is preferable. For this purpose, a material having an appropriate ionization potential, a high hole mobility, and excellent stability is preferable, and impurities such as traps are less likely to be generated during the manufacture and use of such a material. preferable.
  • inorganic compounds such as p-type Si and p-type SiC can be used as the hole transport material.
  • the compound represented by the general formula (1) can be used as a hole transporting material because of its excellent electrochemical stability.
  • a hole injection layer may be provided between the anode and the hole transport layer. By providing the hole injection layer, the light emitting element is driven at a lower voltage, and the durability life is also improved.
  • a material having an ionization potential smaller than that of a material usually used for the hole transport layer is preferably used. Specific examples include benzidine derivatives such as TPD232, starburst arylamine materials, phthalocyanine derivatives, and the like.
  • the hole injection layer is composed of an acceptor compound alone or a structure in which the acceptor compound is doped with another hole injection material.
  • acceptor compounds include metal chlorides such as iron (III) chloride, aluminum chloride, gallium chloride, indium chloride, antimony chloride, metal oxides such as molybdenum oxide, vanadium oxide, tungsten oxide, ruthenium oxide, A charge transfer complex such as tris (4-bromophenyl) aminium hexachloroantimonate (TBPAH).
  • organic compounds having a nitro group, a cyano group, a halogen atom, or a trifluoromethyl group in the molecule quinone compounds, acid anhydride compounds, fullerenes, and the like are also included.
  • these compounds include hexacyanobutadiene, hexacyanobenzene, tetracyanoethylene, tetracyanoquinodimethane (TCNQ), tetrafluorotetracyanoquinodimethane (F 4 -TCNQ), 2, 3, 6, 7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN 6 ), p-fluoranyl, p-chloranil, p-bromanyl, p-benzoquinone, 2,6- Dichlorobenzoquinone, 2,5-dichlorobenzoquinone, tetramethylbenzoquinone, 1,2,4,5-tetracyanobenzene, o-dicyanobenzene, p-dicyanobenzene, 1,4-dicyano-2,3,5,6- Tetrafluorobenzene, 2,3-dichloro-5,6-dicyanobenz
  • the hole injection layer is composed of the acceptor compound alone and when the hole injection material is doped with the acceptor compound, the hole injection layer may be a single layer, A plurality of layers may be laminated.
  • the hole injection material used in combination when the acceptor compound is doped is the same compound as the compound used for the hole transport layer from the viewpoint that the hole injection barrier to the hole transport layer can be relaxed. More preferably.
  • the light emitting layer may be either a single layer or a plurality of layers, and each is formed of a light emitting material (host material, dopant material).
  • the light emitting layer may be a mixture of a host material and a dopant material or a host material alone. That is, in the organic thin film light emitting device according to the embodiment of the present invention, only the host material or the dopant material may emit light in each light emitting layer, or both the host material and the dopant material may emit light. From the viewpoint of efficiently using electric energy and obtaining light emission with high color purity, the light emitting layer is preferably composed of a mixture of a host material and a dopant material.
  • the host material and the dopant material may be either one kind or a plurality of combinations.
  • the dopant material may be included in the entire host material or may be partially included.
  • the dopant material may be laminated or dispersed.
  • the emission color of the light-emitting element can be controlled by the type of the dopant material. If the amount of the dopant material is too large, a concentration quenching phenomenon occurs, so that it is preferably used at 20% by weight or less, more preferably 10% by weight or less with respect to the host material.
  • the doping method may be a co-evaporation method with a host material, or may be vapor-deposited simultaneously after mixing with the host material in advance.
  • the light emitting material is not particularly limited, and specifically, metal chelation such as fused ring derivatives such as anthracene and pyrene, tris (8-quinolinolate) aluminum (III), which have been known as light emitters.
  • metal chelation such as fused ring derivatives such as anthracene and pyrene, tris (8-quinolinolate) aluminum (III), which have been known as light emitters.
  • Oxinoid compounds bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives; tetraphenylbutadiene derivatives, indene derivatives, coumarin derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, oxadiazole derivatives, thiols Asiazolopyridine derivatives, dibenzofuran derivatives, carbazole derivatives, indolocarbazole derivative
  • the host material is not particularly limited, but is a compound having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, chrysene, naphthacene, triphenylene, perylene, fluoranthene, fluorene, indene, or a derivative thereof; N, N′-dinaphthyl- Aromatic amine derivatives such as N, N′-diphenyl-4,4′-diphenyl-1,1′-diamine; metal chelated oxinoid compounds including tris (8-quinolinolate) aluminum (III); distyrylbenzene Bisstyryl derivatives such as derivatives; tetraphenylbutadiene derivatives, indene derivatives, coumarin derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, perinone derivatives, cyclopentadiene derivatives, pyrrolopyrrole derivatives
  • the LUMO energy level is close to that of the compound represented by the general formula (1), and electron injection is likely to occur.
  • a compound having an anthracene skeleton is more preferable.
  • the dopant material is a compound having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, chrysene, triphenylene, perylene, fluoranthene, fluorene, indene or a derivative thereof (for example, 2- (benzothiazol-2-yl ) -9,10-diphenylanthracene and 5,6,11,12-tetraphenylnaphthacene); furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, Compounds having heteroaryl rings such as benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyridine, pyrazine, naphthyridine, quinoxaline
  • the light emitting layer may contain a phosphorescent material.
  • a phosphorescent material is a material that exhibits phosphorescence even at room temperature.
  • the phosphorescent material is not particularly limited, but iridium (Ir), ruthenium (Ru), rhodium (Rh), palladium (Pd), platinum (Pt), osmium (Os), and rhenium (Re).
  • Examples of host materials used in combination with a phosphorescent dopant material include indole derivatives, carbazole derivatives, indolocarbazole derivatives; nitrogen-containing aromatic compound derivatives having a pyridine, pyrimidine, or triazine skeleton; polyarylbenzene derivatives, spiro And aromatic hydrocarbon compound derivatives such as fluorene derivatives, truxene derivatives and triphenylene derivatives; compounds containing chalcogen elements such as dibenzofuran derivatives and dibenzothiophene derivatives; organometallic complexes such as beryllium quinolinol complexes; and the like.
  • the host material is not limited to these as long as it has triplet energy larger than that of the dopant material to be used, and electrons and holes are smoothly injected and transported from the respective transport layers.
  • the light emitting layer may contain two or more phosphorescent dopant materials, and may contain two or more host materials. Further, one or more phosphorescent dopants and one or more fluorescent dopant materials may be contained.
  • a phosphorescent material is used for the light emitting layer, the compound represented by the general formula (1) is preferably used as an electron transporting material.
  • the compound represented by the general formula (1) Since the compound represented by the general formula (1) has high light emission performance, it can also be used as a light emitting material. Since the compound represented by the general formula (1) exhibits strong light emission in the blue to green region (400 to 600 nm region), it can be suitably used as a blue and green light emitting material. Since the compound represented by the general formula (1) has a high fluorescence quantum yield, it is suitably used as a fluorescent dopant material. Further, the carbazole skeleton and the quinazoline skeleton have high triplet excitation energy levels, and the compound represented by the general formula (1) can be preferably used as a phosphorescent host material. In particular, it can be suitably used for a green phosphorescent host material and a red phosphorescent host material.
  • the preferred phosphorescent host or dopant is not particularly limited, but specific examples include the following.
  • the light emitting layer may contain a heat activated delayed fluorescent material.
  • Thermally activated delayed fluorescent materials are also commonly referred to as TADF materials. Thermally activated delayed fluorescent material promotes reverse intersystem crossing from triplet excited state to singlet excited state by reducing the energy gap between singlet excited state energy level and triplet excited state energy level In addition, this is a material in which the generation probability of singlet excitons is improved.
  • the thermally activated delayed fluorescent material may be a material that exhibits thermally activated delayed fluorescence with a single material, or may be a material that exhibits thermally activated delayed fluorescence with a plurality of materials. When a plurality of materials are used, they may be used as a mixture or may be used by stacking layers made of the respective materials.
  • thermally activated delayed fluorescent material A known material can be used as the thermally activated delayed fluorescent material. Specific examples include, but are not limited to, benzonitrile derivatives, triazine derivatives, disulfoxide derivatives, carbazole derivatives, indolocarbazole derivatives, dihydrophenazine derivatives, thiazole derivatives, oxadiazole derivatives, and the like. Absent.
  • the electron transport layer is a layer between the cathode and the light emitting layer.
  • the electron transport layer may be a single layer or a plurality of layers, and may or may not be in contact with the cathode or the light emitting layer. It is preferable that the electron transport layer is composed of two or more layers, and the compound represented by the general formula (1) is contained on the side in contact with the light emitting layer.
  • the compound represented by the general formula (1) easily receives electrons from a compound having a pyrene skeleton, a phenanthroline skeleton, or a fluoranthene skeleton. It is preferable to contain a compound having a phenanthroline skeleton, a pyrene skeleton, or a fluoranthene skeleton.
  • the electron transport layer is desired to have high electron injection efficiency from the cathode, to efficiently transport injected electrons, and high electron injection efficiency to the light emitting layer. Therefore, the material constituting the electron transport layer is preferably a material having a high electron affinity, a high electron mobility, and excellent stability. In addition, it is preferable that impurities that become traps are less likely to be generated during the manufacture and use of such materials.
  • the electron transport layer plays a role in efficiently blocking the flow to the cathode side. It is also preferable. In this case, even if the electron transport layer is made of a material that does not have a high electron transport capability, the effect of improving the light emission efficiency of the light emitting element is that the electron transport layer is made of a material having a high electron transport capability. It becomes equivalent. Therefore, the electron transport layer in the present invention includes a hole blocking layer that can efficiently block the movement of holes as the same meaning.
  • the electron transport material used for the electron transport layer is not particularly limited, and examples thereof include condensed polycyclic aromatic hydrocarbon derivatives such as naphthalene and anthracene, and 4,4′-bis (diphenylethenyl) biphenyl.
  • Stylyl aromatic ring derivatives quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, quinolinol complexes such as tris (8-quinolinolate) aluminum (III), benzoquinolinol complexes, hydroxyazole complexes, azomethine complexes, tropolone metal complexes and flavonols
  • quinolinol complexes such as tris (8-quinolinolate) aluminum (III), benzoquinolinol complexes, hydroxyazole complexes, azomethine complexes, tropolone metal complexes and flavonols
  • Examples include various metal complexes such as metal complexes.
  • the electron transport material is composed of an element selected from carbon, hydrogen, nitrogen, oxygen, silicon and phosphorus, and electron accepting nitrogen is used. It is preferable to use a compound having a heteroaryl ring structure.
  • aromatic heterocycles containing electron-accepting nitrogen examples include pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, quinoxaline ring, naphthyridine ring, pyrimidopyrimidine ring, benzoquinoline ring, phenanthroline ring, imidazole ring, oxazole ring Oxadiazole ring, triazole ring, thiazole ring, thiadiazole ring, benzoxazole ring, benzothiazole ring, benzimidazole ring, phenanthrimidazole ring and the like.
  • the electron transport material may be used alone, but two or more of the electron transport materials may be used in combination, or one or more of the other electron transport materials may be used in combination with the electron transport material. .
  • the preferred electron transport material is not particularly limited, but specific examples include the following.
  • the compound represented by the general formula (1) can also be used as an electron transporting material because it has a high electron injecting and transporting ability.
  • the compound represented by the general formula (1) it is not necessary to be limited to only one of them, and a plurality of types of the compound represented by the general formula (1) may be mixed and used.
  • One or more kinds of other electron transport materials such as the above and a compound represented by the general formula (1) may be mixed and used.
  • the electron transport layer may contain a donor material in addition to the electron transport material.
  • the donor material is a compound that facilitates electron injection from the cathode or the electron injection layer to the electron transport layer by improving the electron injection barrier and further improves the electrical conductivity of the electron transport layer.
  • Preferred examples of the donor material in the present invention include an alkali metal, an inorganic salt containing an alkali metal, a complex of an alkali metal and an organic material, an alkaline earth metal, an inorganic salt containing an alkaline earth metal, or an alkaline earth metal And a complex of organic substance.
  • Preferable types of alkali metals and alkaline earth metals include alkali metals such as lithium, sodium and cesium, which have a low work function and a large effect of improving the electron transport ability, and alkaline earth metals such as magnesium and calcium.
  • an inorganic salt or a complex of a metal and an organic substance is preferable to a simple metal. Furthermore, it is more preferably a complex of a metal and an organic substance in terms of easy handling in the air and ease of controlling the addition concentration.
  • inorganic salts include oxides such as LiO and Li 2 O, nitrides, fluorides such as LiF, NaF, and KF, Li 2 CO 3 , Na 2 CO 3 , K 2 CO 3 , Rb 2 CO 3 , And carbonates such as Cs 2 CO 3 .
  • a preferable example of the alkali metal or alkaline earth metal is lithium from the viewpoint that the raw materials are inexpensive and easy to synthesize.
  • organic substance in the complex of metal and organic substance include quinolinol, benzoquinolinol, flavonol, hydroxyimidazopyridine, hydroxybenzazole, hydroxytriazole and the like.
  • a complex of an alkali metal and an organic substance is preferable, a complex of lithium and an organic substance is more preferable, and lithium quinolinol is particularly preferable. Two or more of these donor materials may be mixed and used.
  • the preferred doping concentration varies depending on the material and the film thickness of the doping region.
  • the deposition rate ratio is more preferably 100: 1 to 5: 1, and further preferably 100: 1 to 10: 1.
  • the deposition rate ratio is more preferably 10: 1 to 1:10, and even more preferably 7: 3 to 3: 7.
  • the electron transport layer in which the compound represented by the general formula (1) is doped with a donor material may be used as a charge generation layer in a tandem light-emitting element that connects a plurality of light-emitting elements.
  • the layer can be suitably used as a charge generation layer.
  • An electron injection layer may be provided between the cathode and the electron transport layer. Generally, the electron injection layer is inserted for the purpose of assisting injection of electrons from the cathode to the electron transport layer.
  • a compound having a heteroaryl ring structure containing electron-accepting nitrogen may be used, or a layer containing the above donor material may be used.
  • the compound represented by the general formula (1) may be included in the electron injection layer.
  • an insulator or a semiconductor inorganic material can be used for the electron injection layer. Use of these materials is preferable because a short circuit of the light emitting element can be effectively prevented and the electron injection property can be improved.
  • At least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides may be used. preferable.
  • a complex of an organic substance and a metal which is a donor material
  • the organic substance in such a complex include quinolinol, benzoquinolinol, pyridylphenol, flavonol, hydroxyimidazopyridine, hydroxybenzazole, hydroxytriazole and the like.
  • a complex of an alkali metal and an organic substance is preferable, a complex of lithium and an organic substance is more preferable, and lithium quinolinol is particularly preferable.
  • each layer constituting the light emitting element is not particularly limited, such as resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, coating method, etc., but resistance heating vapor deposition or electron beam vapor deposition is usually used in terms of element characteristics. preferable.
  • the thickness of the organic layer is not limited because it depends on the resistance value of the luminescent material, but is preferably 1 to 1000 nm.
  • the film thicknesses of the light emitting layer, the electron transport layer, and the hole transport layer are each preferably 1 nm to 200 nm, and more preferably 5 nm to 100 nm.
  • the organic thin film light emitting device has a function of converting electrical energy into light.
  • a direct current is mainly used as electric energy, but a pulse current or an alternating current can also be used.
  • the current value and the voltage value are not particularly limited, but are preferably selected so that the maximum luminance can be obtained with as low energy as possible in consideration of the power consumption and lifetime of the element.
  • the organic thin film light emitting element according to the embodiment of the present invention is suitably used as a display device such as a display that displays in a matrix and / or segment system, for example.
  • the matrix method is a method in which pixels for display are two-dimensionally arranged such as a lattice shape or a mosaic shape, and a character or an image is displayed by a set of pixels.
  • the shape and size of the pixel are determined by the application. For example, a square pixel with a side of 300 ⁇ m or less is usually used for displaying images and characters on a personal computer, monitor, TV, and a pixel with a side of mm order for a large display such as a display panel. become.
  • monochrome display pixels of the same color may be arranged. However, in color display, red, green, and blue pixels are displayed side by side. In this case, there are typically a delta type and a stripe type.
  • the matrix driving method may be either a line sequential driving method or an active matrix. Although the structure of the line sequential drive is simple, the active matrix may be superior in consideration of the operation characteristics.
  • the segment method is a method in which a pattern is formed so as to display predetermined information and a region determined by the arrangement of the pattern is caused to emit light.
  • Examples of the display using the segment method include time and temperature display on a digital clock and a thermometer, operation status display of an audio device, an electromagnetic cooker, and the like, and an automobile panel display.
  • the matrix method and the segment method may coexist in the same panel.
  • the organic thin film light emitting device is preferably used as a backlight for various devices.
  • the backlight is used mainly for the purpose of improving the visibility of a display device that does not emit light, and is used for a liquid crystal display device, a clock, an audio device, an automobile panel, a display panel, a sign, and the like.
  • the organic thin film light emitting element of the present invention is preferably used for a liquid crystal display device, particularly a backlight for a personal computer for which a reduction in thickness is being considered, and a backlight that is thinner and lighter than conventional ones can be provided.
  • the organic thin film light-emitting element according to the embodiment of the present invention is preferably used as an illumination device such as organic EL illumination.
  • the organic EL lighting is used for general lighting, exhibition lighting, automobile tail lamps, and the like, and the organic thin film light emitting device of the present invention is suitably used for these.
  • the obtained yellowish white solid was confirmed to be compound [1] by mass spectrum measurement (JMS-Q1000TD manufactured by JEOL Ltd.).
  • Compound [1] was used as a light emitting device material after sublimation purification at about 330 ° C. under a pressure of 1 ⁇ 10 ⁇ 3 Pa using an oil diffusion pump.
  • the obtained yellowish white solid was confirmed to be the compound [2] by mass spectrum measurement (JMS-Q1000TD manufactured by JEOL Ltd.).
  • Compound [2] was used as a light emitting device material after sublimation purification at about 330 ° C. under a pressure of 1 ⁇ 10 ⁇ 3 Pa using an oil diffusion pump.
  • intermediate [E] was purified by silica gel column chromatography using a heptane-toluene mixed developing solvent.
  • the obtained yellowish white solid was confirmed to be compound [3] by mass spectrum measurement (JMS-Q1000TD, manufactured by JEOL Ltd.).
  • Compound [3] was used as a light emitting device material after sublimation purification at about 350 ° C. under a pressure of 1 ⁇ 10 ⁇ 3 Pa using an oil diffusion pump.
  • Example 1 A glass substrate (manufactured by Geomat Co., Ltd., 11 ⁇ / ⁇ , sputtered product) on which an ITO transparent conductive film was deposited at 165 nm was cut into a size of 38 ⁇ 46 mm and etched. The obtained substrate was ultrasonically cleaned with “Semico Clean 56” (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes and then with ultrapure water. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the light-emitting element, placed in a vacuum vapor deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 ⁇ 10 ⁇ 4 Pa or less.
  • “Semico Clean 56” trade name, manufactured by Furuuchi Chemical Co., Ltd.
  • HAT-CN 6 was deposited as a hole injection layer by 5 nm by a resistance heating method, and then HT-1 was deposited as a hole transport layer by 50 nm.
  • a mixed layer of the host material H-1 and the dopant material D-1 was deposited as a light emitting layer to a thickness of 20 nm so that the doping concentration was 5 wt%.
  • Compound [1] was vapor-deposited to a thickness of 35 nm as an electron transport layer.
  • lithium fluoride was deposited to a thickness of 0.5 nm, and then aluminum was deposited to a thickness of 1000 nm to form a cathode, thereby producing a 5 ⁇ 5 mm square light-emitting element.
  • the film thickness referred to here is a display value of a crystal oscillation type film thickness monitor, and is common to other examples and comparative examples.
  • this light-emitting element was lit at a luminance of 1000 cd / m 2
  • the driving voltage was 4.11 V
  • the external quantum efficiency was 5.63%.
  • the initial luminance was set to 1000 cd / m 2 and driven at a constant current
  • the time (durability) during which the luminance decreased by 20% was 1020 hours.
  • Compound [1] HAT-CN 6 , HT-1, H-1, and D-1 are the compounds shown below.
  • Examples 2-32 A light emitting device was prepared and evaluated in the same manner as in Example 1 except that the compounds listed in Table 1 were used for the electron transport layer. The results are shown in Table 1. Compounds [2] to [32] are the compounds shown below.
  • Comparative Examples 1-12 A light emitting device was prepared and evaluated in the same manner as in Example 1 except that the compounds listed in Table 1 were used for the electron transport layer. The results are shown in Table 1. E-1 to E-12 are the compounds shown below.
  • Example 33 A glass substrate (manufactured by Geomat Co., Ltd., 11 ⁇ / ⁇ , sputtered product) on which an ITO transparent conductive film was deposited at 165 nm was cut into a size of 38 ⁇ 46 mm and etched. The obtained substrate was ultrasonically cleaned with “Semico Clean 56” (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes and then with ultrapure water. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the light-emitting element, placed in a vacuum vapor deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 ⁇ 10 ⁇ 4 Pa or less.
  • “Semico Clean 56” trade name, manufactured by Furuuchi Chemical Co., Ltd.
  • HAT-CN 6 was deposited as a hole injection layer by 5 nm by a resistance heating method, and then HT-1 was deposited as a hole transport layer by 40 nm. Next, 10 nm of HT-2 was deposited as a blue hole transport layer. Next, a mixed layer of the host material H-1 and the dopant material D-1 was deposited as a light emitting layer to a thickness of 20 nm so that the doping concentration was 5 wt%. Next, the compound [1] was deposited to a thickness of 25 nm as a first electron transport layer.
  • compound E-13 is used as the electron transport material
  • 2E-1 is used as the donor material
  • lithium fluoride was deposited to a thickness of 0.5 nm
  • aluminum was deposited to a thickness of 1000 nm to form a cathode, thereby producing a 5 ⁇ 5 mm square light-emitting element.
  • this light-emitting element was lit at a luminance of 1000 cd / m 2
  • the driving voltage was 3.97 V and the external quantum efficiency was 6.30%.
  • the initial luminance was set to 1000 cd / m 2 and driving at constant current, the time for the luminance to decrease by 20% was 1710 hours.
  • HT-2, E-13, and 2E-1 are the compounds shown below.
  • Examples 34 to 50 A light emitting device was fabricated and evaluated in the same manner as in Example 33 except that the compounds described in Table 2 were used for the host material and the first electron transport layer, respectively. The results are shown in Table 2.
  • H-2 and H-3 are the compounds shown below.
  • Comparative Examples 13 to 48 A light emitting device was fabricated and evaluated in the same manner as in Example 21 except that the compounds listed in Table 2 were used for the host material and the first electron transport layer, respectively. The results are shown in Table 2.
  • Example 51 A glass substrate (manufactured by Geomat Co., Ltd., 11 ⁇ / ⁇ , sputtered product) on which an ITO transparent conductive film was deposited at 165 nm was cut into a size of 38 ⁇ 46 mm and etched. The obtained substrate was ultrasonically cleaned with “Semico Clean 56” (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes and then with ultrapure water. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the light-emitting element, placed in a vacuum vapor deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 ⁇ 10 ⁇ 4 Pa or less.
  • “Semico Clean 56” trade name, manufactured by Furuuchi Chemical Co., Ltd.
  • HAT-CN 6 was deposited as a hole injection layer by 5 nm by a resistance heating method, and then HT-1 was deposited as a hole transport layer by 40 nm. Next, 10 nm of HT-2 was deposited as a blue hole transport layer. Next, a mixed layer of the host material H-1 and the dopant material D-1 was deposited as a light emitting layer to a thickness of 20 nm so that the doping concentration was 5 wt%. Next, the compound [1] was deposited to a thickness of 25 nm as a first electron transport layer.
  • compound E-14 is used as the electron transport material
  • 2E-1 is used as the donor material
  • a 5 ⁇ 5 mm square device was fabricated.
  • this light-emitting element was lit at a luminance of 1000 cd / m 2
  • the driving voltage was 4.21 V
  • the external quantum efficiency was 7.52%.
  • the initial luminance was set to 1000 cd / m 2 and driving at constant current, the time for the luminance to decrease by 20% was 2050 hours.
  • E-14 is a compound shown below.
  • Examples 52-68 A light emitting device was prepared and evaluated in the same manner as in Example 51 except that the compounds described in Table 3 were used as the first electron transport layer and the second electron transport layer, respectively. The results are shown in Table 3. E-15 and E-16 are the compounds shown below.
  • Comparative Examples 49-84 A light emitting device was prepared and evaluated in the same manner as in Example 51 except that the compounds described in Table 3 were used as the first electron transport layer and the second electron transport layer, respectively. The results are shown in Table 3.
  • Example 69 A glass substrate (manufactured by Geomat Co., Ltd., 11 ⁇ / ⁇ , sputtered product) on which an ITO transparent conductive film was deposited by 90 nm was cut into 38 ⁇ 46 mm and etched. The obtained substrate was ultrasonically cleaned with “Semico Clean 56” (trade name, manufactured by Furuuchi Chemical Co., Ltd.) for 15 minutes and then with ultrapure water. This substrate was subjected to UV-ozone treatment for 1 hour immediately before producing the device, placed in a vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus became 5 ⁇ 10 ⁇ 4 Pa or less. HAT-CN 6 was deposited as a hole injection layer by a resistance heating method to a thickness of 10 nm.
  • HT-1 was deposited to 110 nm as the first hole transport layer.
  • 20 nm of compound HT-2 was deposited as a second hole transport layer.
  • Compound H-4 was used as the host material
  • Compound D-2 was used as the dopant material
  • the dopant material was deposited to a thickness of 40 nm so that the doping concentration was 10 wt%.
  • the compound [1] was deposited to a thickness of 25 nm as a first electron transport layer.
  • a cathode a 5 ⁇ 5 mm square element was produced.
  • the film thickness referred to here is a crystal oscillation type film thickness monitor display value.
  • the effective efficiency (lm / W) is the front luminance (cd / cm 2 ) obtained by measurement with a spectral radiance meter (CS-1000, manufactured by Konica Minolta), and the power density (W / cm 2 ) input to the device. 2 ) and the radiation angle (sr, steradian).
  • CS-1000 spectral radiance meter
  • W / cm 2 power density
  • Examples 70-74 A light emitting device was prepared and evaluated in the same manner as in Example 69 except that the compounds listed in Table 4 were used for the first electron transport layer. The results are shown in Table 4.
  • Comparative Examples 85-96 A light emitting device was prepared and evaluated in the same manner as in Example 69 except that the compounds described in Table 4 were used for the first electron transport layer. The results are shown in Table 4.

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  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Devices For Indicating Variable Information By Combining Individual Elements (AREA)
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Abstract

L'objectif de la présente invention est de fournir un élément électroluminescent à film mince organique qui est amélioré du point de vue : efficacité lumineuse, tension de commande et durée de vie. La présente invention concerne un composé spécifique contenant un squelette de quinazoline.
PCT/JP2018/010824 2017-03-28 2018-03-19 Composé, dispositif électronique le contenant, élément électroluminescent à film mince organique, dispositif d'affichage et dispositif d'éclairage WO2018180709A1 (fr)

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JP2018515691A JP6954275B2 (ja) 2017-03-28 2018-03-19 化合物、それを含有する電子デバイス、有機薄膜発光素子、表示装置および照明装置
KR1020197026760A KR102514842B1 (ko) 2017-03-28 2018-03-19 화합물, 그것을 함유하는 전자 디바이스, 유기 박막 발광 소자, 표시 장치 및 조명 장치
CN201880017449.5A CN110392682B (zh) 2017-03-28 2018-03-19 化合物、含有该化合物的电子器件、有机薄膜发光元件、显示装置及照明装置

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JP6954275B2 (ja) 2021-10-27
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